1014
H. Schedel and K. Burger
J 7 Hz, 1H, NCH) ppm; 13C NMR (50 MHz, CDCl3): ꢁ 14:40 (CH3Et), 18.39 (CH3), 40.82
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1
(CH2), 54.67 (CH), 90.19 (m, CCF3), 120.98 (q, JCF 288 Hz, CF3), 122.22 (q, JCF 294 Hz,
CF3), 171.53 (CO) ppm; 19F NMR (188 MHz, CDCl3): ꢁ 0:92 (q, JFF 8 Hz, CF3), 3.24 (q,
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4JFF 8 Hz, CF3) ppm; IR (®lm): ꢂ 1839 cm 1; EI-MS: m=zꢁ% 265 (20, M ), 250 (14), 218
(10), 196 (30), 168 (100), 140 (27), 70 (16), 69 (32), 56 (64).
(4S)-3-Ethyl-2,2-bis-(tri¯uoromethyl)-4-isopropyloxazolidin-5-one (7; C10H13F6NO2)
2 (5.5 g, 17.5 mmol) gave 7 (3.1 g, 60%) as a colorless, slightly rancid smelling, oily liquid.
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D
1
B.p.: 82ꢀC/16.0 torr; ꢀ 33 (c 2, CH2Cl2); H NMR (200 MHz, CDCl3): ꢁ 0:99 (d,
J 7 Hz, 3H, CH3), 1.17 (t, J 7 Hz, 3H, CH3Et), 1.19 (d, J 7 Hz, 3H, CH3), 2.17 (m, 1H, CH), 3.05
(m, 1H, CH2), 3.27 (m, 1H, CH2), 3.71 (m, 1H, NCH) ppm; 13C NMR (50 MHz, CDCl3) ꢁ 13:67
(CH3Et), 15.61 (CH3), 17.86 (CH3), 29.72 (CH), 40.88 (CH2), 63.80 (NCH), 89.03 (m, CCF3), 121.08 (q,
1JCF 289 Hz, CF3), 122.68 (q, 1JCF 296 Hz, CF3), 169.14 (CO) ppm; 19F NMR (188 MHz, CDCl3)
ꢁ 0:16 (q, 4JFF 8 Hz, CF3), 4.01 (q, 4JFF 8 Hz, CF3) ppm; IR (®lm): ꢂ 1833 cm 1; EI-MS:
m=zꢁ% 293 (9, M ), 251 (56), 250 (34), 222 (15), 182 (100), 154 (11), 56 (22).
(4S)-3-Ethyl-2,2-bis-(tri¯uoromethyl)-4-isobutyloxazolidin-5-one (8; C11H15F6NO2)
3 (5.6 g, 17.5 mmol) gave 8 (3.1 g, 58%) as a colorless, rancid smelling, oily liquid.
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B.p.: 87ꢀC/15.0 torr; ꢀ 44 (c 2, CH2Cl2); 1H NMR (200MHz, CDCl3): ꢁ 0:93 (d,
D
J 7 Hz, 3H, CH3), 0.97 (d, J 7 Hz, 3H, CH3), 1.18 (t, J 7 Hz, 3H, CH3Et), 1.66±1.73 (m, 2H,
CH2), 2.01 (m, 1H, CH), 3.06 (m, 1H, NCH2), 3.24 (m, 1H, NCH2), 3.79 (m, 1H, NCH) ppm; 13C
NMR (50 MHz, CDCl3) ꢁ 13:81 (CH3Et), 22.07 (CH3), 23.99 (CH3), 24.05 (CH), 40.36 (CH2), 40.73
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(CH2), 56.83 (NCH), 90.03 (m, CCF3), 121.08 (q, JCF 288 Hz, CF3), 122.36 (q, JCF 295 Hz,
CF3), 171.02 (CO) ppm; 19F NMR (188MHz, CDCl3): ꢁ 0:50 (q, JFF 9 Hz, CF3), 3.48 (q,
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4JFF 9 Hz, CF3) ppm; IR (®lm): ꢂ 1837 cm 1; EI-MS: m=zꢁ% 307 (25, M ), 260 (11), 251
(39), 250 (100), 238 (26), 236 (18), 222 (54), 210 (44), 182 (49), 154 (19), 69 (22), 57 (18), 56 (54).
(4R)-3-Ethyl-2,2-bis-(tri¯uoromethyl)-4-phenyloxazolidin-5-one (9; C13H11F6NO2)
4 (6.1 g, 17.5 mmol) gave 9 (2.9 g, 50%) as a colorless, resinously smelling, oily liquid.
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D
1
M.p.: 40ꢀC; b.p.: 72ꢀC/0.6 torr; ꢀ
111 (c 2, CH2Cl2); ee 89% (HPLC); H NMR
(200 MHz, CDCl3): ꢁ 0:86 (t, J 7 Hz, 3H, CH3), 3.09 (m, 1H, CH2), 3.29 (m, 1H, CH2), 4.69 (s,
1H, CH), 7.41 (m, 5H, arom. H) ppm; 13C NMR (50 MHz, CDCl3): ꢁ 14:10 (CH3), 42.56 (CH2),
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64.24 (CH), 90.16 (m, CCF3), 121.24 (q, JCF 289Hz, CF3), 122.52 (q, JCF 295 Hz, CF3),
128.21, 129.69, 130.04, 136.01 (arom. C), 168.96 (CO) ppm; 19F NMR (188 MHz, CDCl3):
ꢁ 0:37 (q, 4JFF 8 Hz, CF3), 4.23 (q, 4JFF 8 Hz, CF3) ppm; IR (®lm): ꢂ 1842 cm 1; EI-MS:
m=zꢁ% 327 (43, M ), 312 (15), 280 (11), 258 (56), 251 (11), 250 (28), 231 (12), 230 (99), 222
(11), 191 (14), 182 (13), 132 (15), 124 (100), 118 (46), 110 (16), 107 (11), 105 (10), 104 (15), 91
(30), 90 (16), 89 (17), 79 (17), 77 (21), 69 (20), 59 (17).
(4S)-3-Ethyl-2,2-bis-(tri¯uoromethyl)-4-phenyloxazolidin-5-one (10; C13H11F6NO2)
5 (6.1 g, 17.5 mmol) gave 10 (2.4 g, 42%) as a colorless, odourless, oily liquid.
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B.p.: 62ꢀC/0.3 torr; ꢀ 97 (c 2, CH2Cl2); ee 88% (HPLC); 1H NMR (200 MHz,
D
CDCl3): ꢁ 0:86 (t, J 7 Hz, 3H, CH3), 3.09 (m, 1H, CH2), 3.28 (m, 1H, CH2), 4.68 (s, 1H, CH),
7.41 (s, 5H, arom. H) ppm; 13C NMR (50 MHz, CDCl3): ꢁ 14:22 (CH3), 42.63 (CH2), 64.29 (CH),
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90.22 (m, CCF3), 121.16 (q, JCF 287 Hz, CF3), 122.46 (q, JCF 295 Hz, CF3), 128.15, 129.63,
129.98, 135.95 (arom. C), 168.83 (CO) ppm; 19F NMR (188 MHz, CDCl3): ꢁ 0:38 (q,
4JFF 8 Hz, CF3), 4.22 (q, JFF 8 Hz, CF3) ppm; IR (®lm): ꢂ 1843 cm 1; EI-MS:
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